Preparation and structural elucidation of (−)-tetrahydroberberine-(+)-2,3-di( p-toluyl) tartaric acid complex

A new (2:1) complex of (−)-13a S-tetrahydroberberine [(−)-13a S-THB] with (+)-2,3-di( p-toluyl) tartaric acid (DTTA), i.e. 5,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-methylenedioxy- 6H dibenzo[a,g] quinolizine·2,3-di( p-toluyl) tartaric acid [2C 20H 20NO 4·C 20H 18O 8], as well as its optical active c...

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Bibliographic Details
Published in:Journal of molecular structure 2008-12, Vol.892 (1), p.466-469
Main Authors: Gao, Jin-Ming, Liu, Wei-Tao, Li, Man-Lin, Liu, Han-Wei, Zhang, Xing-Chang, Li, Zong-Xiao
Format: Article
Language:English
Subjects:
(+)-2,3-Di( p-toluyl) tartaric acid
(−)-13a S-Tetrahydroberberine
Complex
Crystal structure
Diffraction
Protoberberine
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Summary:A new (2:1) complex of (−)-13a S-tetrahydroberberine [(−)-13a S-THB] with (+)-2,3-di( p-toluyl) tartaric acid (DTTA), i.e. 5,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-methylenedioxy- 6H dibenzo[a,g] quinolizine·2,3-di( p-toluyl) tartaric acid [2C 20H 20NO 4·C 20H 18O 8], as well as its optical active component (−)-THB, has been obtained from the resolution process of (±)-THB in methanol. The structures of this complex and an enantiomer (−)-13a S-THB have been characterized by CD, IR and NMR spectroscopy as well as by X-ray single crystal diffraction.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2008.06.013